NPASS Compound

Structure

NPC473654 OpenBabel07101718182D 46 51 0 0 1 0 0 0 0 0999 V2000 1.5058 4.7981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2360 1.6711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8274 1.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7168 2.9450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8265 0.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 -0.0944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8639 1.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1105 -0.5848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8977 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2011 2.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2611 -0.0944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1105 1.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2688 2.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5722 3.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4118 1.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4118 2.3575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7056 0.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8651 0.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4090 3.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0032 3.3067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4766 3.8178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7146 0.8404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2611 0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6060 3.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7074 2.6240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1394 1.7790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0289 2.7535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5624 2.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3048 1.8817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2758 1.7434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5277 3.5697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0759 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9770 3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9281 2.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8848 0.4232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1363 2.8479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1734 -0.0264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5624 3.8287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 4.4102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3142 4.8029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0108 3.7135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7345 0.8765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7130 2.3575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 36 1 0 0 0 0 4 36 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 19 37 1 0 0 0 0 20 23 2 0 0 0 0 21 27 1 0 0 0 0 21 38 1 0 0 0 0 22 43 1 0 0 0 0 23 33 1 0 0 0 0 24 39 2 0 0 0 0 24 44 1 0 0 0 0 26 35 1 0 0 0 0 27 22 1 1 0 0 0 27 32 1 0 0 0 0 28 18 1 1 0 0 0 28 29 1 0 0 0 0 28 36 1 0 0 0 0 29 20 1 1 0 0 0 29 36 1 0 0 0 0 30 40 2 0 0 0 0 30 45 1 0 0 0 0 31 32 1 0 0 0 0 31 34 1 0 0 0 0 31 38 1 1 0 0 0 32 44 1 1 0 0 0 33 38 1 0 0 0 0 33 41 2 0 0 0 0 34 37 1 6 0 0 0 34 46 1 0 0 0 0 35 42 2 0 0 0 0 35 43 1 0 0 0 0 37 5 1 6 0 0 0 37 46 1 0 0 0 0 38 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.29
Volume:	653.149
LogP:	5.867
LogD:	4.466
LogS:	-4.453
# Rotatable Bonds:	10
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	5.315
Fsp3:	0.474
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.024
MDCK Permeability:	2.4947252313722856e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.585

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	98.74365997314453%
Volume Distribution (VD):	1.96
Pgp-substrate:	4.875485420227051%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.506
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.721
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.733

ADMET: Excretion

Clearance (CL):	4.574
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.788
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.969
Carcinogencity:	0.081
Eye Corrosion:	0.004
Eye Irritation:	0.046
Respiratory Toxicity:	0.611

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC473654

Natural Product ID:	NPC473654
*Common Name:**	Latilagascene G
IUPAC Name:	n.a.
Synonyms:	Latilagascene G
Standard InCHIKey:	LJAHHBLEMUGHFM-NSMQPIFPSA-N
Standard InCHI:	InChI=1S/C38H42O8/c1-23-20-29-28(36(29,3)4)18-19-37(5)34(46-37)31-32(44-24(2)39)27(22-43-35(42)26-14-10-7-11-15-26)21-38(31,33(23)41)45-30(40)17-16-25-12-8-6-9-13-25/h6-17,20,27-29,31-32,34H,18-19,21-22H2,1-5H3/b17-16+,23-20+/t27-,28+,29-,31-,32+,34-,37-,38-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@@H](COC(=O)c2ccccc2)C[C@]2([C@H]1[C@H]1O[C@]1(C)CC[C@H]1[C@@H](/C=C(/C2=O)C)C1(C)C)OC(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448193
PubChem CID:	44588950
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18824363]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[6736971]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	8

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	68.9	n.a.	PMID[570230]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	478.3	n.a.	PMID[570230]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	71.6	n.a.	PMID[570230]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	496.6	n.a.	PMID[570230]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	32.2	ug ml-1	PMID[570230]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	28.0	ug ml-1	PMID[570230]
NPT35	Others	n.a.		LogP	=	7.9	n.a.	PMID[570230]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FICI	=	0.14	n.a.	PMID[570230]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC473654 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	1324
0.2-0.3	2588
0.3-0.4	6926
0.4-0.5	12714
0.5-0.6	13495
0.6-0.7	4616
0.7-0.8	504
0.8-0.85	53
0.85-0.9	74
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC276652
0.9697	High Similarity	NPC477358
0.9635	High Similarity	NPC477095
0.9621	High Similarity	NPC270364
0.9559	High Similarity	NPC82467
0.9481	High Similarity	NPC475660
0.9416	High Similarity	NPC477096
0.9416	High Similarity	NPC477094
0.9394	High Similarity	NPC477360
0.9328	High Similarity	NPC265459
0.9328	High Similarity	NPC475262
0.9328	High Similarity	NPC290833
0.9259	High Similarity	NPC194769
0.9259	High Similarity	NPC285221
0.9254	High Similarity	NPC472250
0.9242	High Similarity	NPC42234
0.9242	High Similarity	NPC475452
0.9242	High Similarity	NPC475671
0.9231	High Similarity	NPC477098
0.9231	High Similarity	NPC477100
0.9197	High Similarity	NPC251294
0.9191	High Similarity	NPC86772
0.9155	High Similarity	NPC25484
0.9155	High Similarity	NPC232583
0.9124	High Similarity	NPC272523
0.9124	High Similarity	NPC325805
0.9111	High Similarity	NPC477359
0.9021	High Similarity	NPC477097
0.9021	High Similarity	NPC477101
0.9021	High Similarity	NPC125033
0.9021	High Similarity	NPC477099
0.9014	High Similarity	NPC205389
0.9	High Similarity	NPC153214
0.8993	High Similarity	NPC473497
0.8971	High Similarity	NPC153617
0.8971	High Similarity	NPC477368
0.8955	High Similarity	NPC3450
0.8955	High Similarity	NPC122504
0.8905	High Similarity	NPC232888
0.8905	High Similarity	NPC477367
0.8905	High Similarity	NPC79699
0.8897	High Similarity	NPC477364
0.8865	High Similarity	NPC45307
0.8857	High Similarity	NPC475413
0.8857	High Similarity	NPC474303
0.8815	High Similarity	NPC272946
0.8788	High Similarity	NPC8990
0.8723	High Similarity	NPC242355
0.8723	High Similarity	NPC187566
0.8722	High Similarity	NPC477369
0.8681	High Similarity	NPC170668
0.8676	High Similarity	NPC475508
0.8643	High Similarity	NPC327511
0.8643	High Similarity	NPC205305
0.8633	High Similarity	NPC472247
0.8603	High Similarity	NPC37968
0.8593	High Similarity	NPC477357
0.8582	High Similarity	NPC121268
0.8582	High Similarity	NPC473301
0.8582	High Similarity	NPC53361
0.8561	High Similarity	NPC298547
0.8561	High Similarity	NPC134937
0.8561	High Similarity	NPC324898
0.8551	High Similarity	NPC233860
0.85	High Similarity	NPC279637
0.85	High Similarity	NPC149401
0.8489	Intermediate Similarity	NPC472248
0.8472	Intermediate Similarity	NPC191387
0.8472	Intermediate Similarity	NPC131966
0.8429	Intermediate Similarity	NPC28836
0.8417	Intermediate Similarity	NPC239358
0.8403	Intermediate Similarity	NPC475135
0.8394	Intermediate Similarity	NPC477370
0.8382	Intermediate Similarity	NPC477366
0.8382	Intermediate Similarity	NPC477363
0.837	Intermediate Similarity	NPC477362
0.8369	Intermediate Similarity	NPC200154
0.8344	Intermediate Similarity	NPC70344
0.8321	Intermediate Similarity	NPC477365
0.8312	Intermediate Similarity	NPC55744
0.831	Intermediate Similarity	NPC202729
0.8298	Intermediate Similarity	NPC311492
0.8286	Intermediate Similarity	NPC233692
0.8276	Intermediate Similarity	NPC183540
0.8252	Intermediate Similarity	NPC27721
0.8231	Intermediate Similarity	NPC134131
0.8231	Intermediate Similarity	NPC25043
0.8176	Intermediate Similarity	NPC475552
0.8146	Intermediate Similarity	NPC469647
0.8146	Intermediate Similarity	NPC469648
0.8146	Intermediate Similarity	NPC138641
0.8146	Intermediate Similarity	NPC22571
0.8146	Intermediate Similarity	NPC283875
0.8133	Intermediate Similarity	NPC254558
0.8108	Intermediate Similarity	NPC471107
0.8108	Intermediate Similarity	NPC471162
0.8108	Intermediate Similarity	NPC471100
0.8095	Intermediate Similarity	NPC95449
0.8074	Intermediate Similarity	NPC473243
0.8067	Intermediate Similarity	NPC473403
0.8041	Intermediate Similarity	NPC470231
0.8039	Intermediate Similarity	NPC469456
0.8028	Intermediate Similarity	NPC238370
0.8026	Intermediate Similarity	NPC233581
0.8026	Intermediate Similarity	NPC145649
0.7987	Intermediate Similarity	NPC11410
0.7986	Intermediate Similarity	NPC476599
0.7961	Intermediate Similarity	NPC51602
0.7961	Intermediate Similarity	NPC472398
0.7959	Intermediate Similarity	NPC266374
0.7958	Intermediate Similarity	NPC470278
0.7929	Intermediate Similarity	NPC472706
0.7922	Intermediate Similarity	NPC251139
0.7922	Intermediate Similarity	NPC282239
0.7917	Intermediate Similarity	NPC471911
0.7917	Intermediate Similarity	NPC4242
0.7905	Intermediate Similarity	NPC182869
0.7902	Intermediate Similarity	NPC472394
0.7891	Intermediate Similarity	NPC162613
0.7891	Intermediate Similarity	NPC87934
0.7887	Intermediate Similarity	NPC147561
0.7877	Intermediate Similarity	NPC475373
0.7877	Intermediate Similarity	NPC184109
0.7871	Intermediate Similarity	NPC217091
0.7871	Intermediate Similarity	NPC106895
0.7867	Intermediate Similarity	NPC127857
0.7852	Intermediate Similarity	NPC477894
0.7843	Intermediate Similarity	NPC471103
0.7842	Intermediate Similarity	NPC472704
0.7832	Intermediate Similarity	NPC72915
0.7826	Intermediate Similarity	NPC40138
0.7823	Intermediate Similarity	NPC9905
0.7821	Intermediate Similarity	NPC472393
0.7812	Intermediate Similarity	NPC477491
0.7806	Intermediate Similarity	NPC21410
0.7806	Intermediate Similarity	NPC473670
0.7806	Intermediate Similarity	NPC473611
0.7793	Intermediate Similarity	NPC329913
0.7785	Intermediate Similarity	NPC192658
0.7785	Intermediate Similarity	NPC472546
0.7778	Intermediate Similarity	NPC470245
0.7778	Intermediate Similarity	NPC473214
0.7778	Intermediate Similarity	NPC475569
0.7778	Intermediate Similarity	NPC7095
0.7778	Intermediate Similarity	NPC112216
0.7771	Intermediate Similarity	NPC471102
0.7771	Intermediate Similarity	NPC159692
0.777	Intermediate Similarity	NPC473613
0.777	Intermediate Similarity	NPC211137
0.777	Intermediate Similarity	NPC43241
0.777	Intermediate Similarity	NPC473112
0.777	Intermediate Similarity	NPC472703
0.777	Intermediate Similarity	NPC473060
0.777	Intermediate Similarity	NPC473109
0.777	Intermediate Similarity	NPC4341
0.777	Intermediate Similarity	NPC473758
0.777	Intermediate Similarity	NPC147880
0.777	Intermediate Similarity	NPC184747
0.777	Intermediate Similarity	NPC48017
0.777	Intermediate Similarity	NPC473085
0.777	Intermediate Similarity	NPC476094
0.777	Intermediate Similarity	NPC473081
0.777	Intermediate Similarity	NPC200592
0.7764	Intermediate Similarity	NPC161151
0.7762	Intermediate Similarity	NPC82712
0.7758	Intermediate Similarity	NPC167340
0.7742	Intermediate Similarity	NPC249471
0.7742	Intermediate Similarity	NPC257213
0.7742	Intermediate Similarity	NPC158333
0.7742	Intermediate Similarity	NPC1173
0.7742	Intermediate Similarity	NPC265395
0.7742	Intermediate Similarity	NPC242262
0.7742	Intermediate Similarity	NPC473414
0.7742	Intermediate Similarity	NPC237549
0.7742	Intermediate Similarity	NPC77719
0.7742	Intermediate Similarity	NPC256142
0.7742	Intermediate Similarity	NPC472030
0.7742	Intermediate Similarity	NPC304876
0.7742	Intermediate Similarity	NPC472005
0.7742	Intermediate Similarity	NPC472022
0.774	Intermediate Similarity	NPC473399
0.774	Intermediate Similarity	NPC66761
0.774	Intermediate Similarity	NPC472577
0.774	Intermediate Similarity	NPC17877
0.774	Intermediate Similarity	NPC473216
0.774	Intermediate Similarity	NPC291638
0.774	Intermediate Similarity	NPC195647
0.7727	Intermediate Similarity	NPC96308
0.7727	Intermediate Similarity	NPC306799
0.7727	Intermediate Similarity	NPC101043
0.7724	Intermediate Similarity	NPC472656
0.7712	Intermediate Similarity	NPC250046
0.7712	Intermediate Similarity	NPC60509
0.7712	Intermediate Similarity	NPC76103
0.7712	Intermediate Similarity	NPC81698
0.7712	Intermediate Similarity	NPC476975
0.7712	Intermediate Similarity	NPC473215
0.7703	Intermediate Similarity	NPC170718
0.7703	Intermediate Similarity	NPC472371
0.7703	Intermediate Similarity	NPC472395

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC473654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	862
0.2-0.3	1636
0.3-0.4	3029
0.4-0.5	2236
0.5-0.6	934
0.6-0.7	153
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD7236	Approved
0.7961	Intermediate Similarity	NPD7239	Suspended
0.7622	Intermediate Similarity	NPD7799	Discontinued
0.7552	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7058	Phase 2
0.75	Intermediate Similarity	NPD7057	Phase 3
0.7365	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2182	Approved
0.7181	Intermediate Similarity	NPD7961	Discontinued
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7083	Intermediate Similarity	NPD6287	Discontinued
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2067	Discontinued
0.6978	Remote Similarity	NPD6858	Approved
0.6978	Remote Similarity	NPD7094	Approved
0.697	Remote Similarity	NPD1238	Approved
0.6943	Remote Similarity	NPD4628	Phase 3
0.6936	Remote Similarity	NPD8368	Discontinued
0.6933	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7741	Discontinued
0.6914	Remote Similarity	NPD8407	Phase 2
0.6912	Remote Similarity	NPD6685	Approved
0.6889	Remote Similarity	NPD164	Approved
0.6879	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6599	Discontinued
0.6836	Remote Similarity	NPD8434	Phase 2
0.6786	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3764	Approved
0.6761	Remote Similarity	NPD2629	Approved
0.676	Remote Similarity	NPD8435	Approved
0.6752	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5761	Phase 2
0.6747	Remote Similarity	NPD5760	Phase 2
0.6743	Remote Similarity	NPD6765	Approved
0.6743	Remote Similarity	NPD6764	Approved
0.6733	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6085	Phase 2
0.6728	Remote Similarity	NPD6273	Approved
0.6726	Remote Similarity	NPD7075	Discontinued
0.6713	Remote Similarity	NPD4198	Discontinued
0.6711	Remote Similarity	NPD7008	Discontinued
0.6711	Remote Similarity	NPD1876	Approved
0.6708	Remote Similarity	NPD6799	Approved
0.6691	Remote Similarity	NPD5765	Approved
0.6689	Remote Similarity	NPD3972	Approved
0.6687	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD8360	Approved
0.6647	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6002	Phase 3
0.6645	Remote Similarity	NPD6355	Discontinued
0.6645	Remote Similarity	NPD6832	Phase 2
0.6642	Remote Similarity	NPD1237	Approved
0.6624	Remote Similarity	NPD7305	Phase 1
0.6623	Remote Similarity	NPD7713	Phase 3
0.66	Remote Similarity	NPD5667	Approved
0.6599	Remote Similarity	NPD17	Approved
0.6592	Remote Similarity	NPD6785	Approved
0.6592	Remote Similarity	NPD6784	Approved
0.6587	Remote Similarity	NPD6801	Discontinued
0.6582	Remote Similarity	NPD7137	Phase 2
0.6582	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD9545	Approved
0.6571	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1930	Approved
0.6569	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1929	Approved
0.6564	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8150	Discontinued
0.6541	Remote Similarity	NPD8485	Approved
0.6541	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5585	Approved
0.6528	Remote Similarity	NPD5951	Approved
0.6509	Remote Similarity	NPD5402	Approved
0.6509	Remote Similarity	NPD3817	Phase 2
0.6485	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5403	Approved
0.6475	Remote Similarity	NPD5048	Discontinued
0.6467	Remote Similarity	NPD6637	Approved
0.6467	Remote Similarity	NPD1608	Approved
0.6466	Remote Similarity	NPD1202	Approved
0.6463	Remote Similarity	NPD5401	Approved
0.6449	Remote Similarity	NPD6647	Phase 2
0.6438	Remote Similarity	NPD2353	Approved
0.6438	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5763	Approved
0.6438	Remote Similarity	NPD5762	Approved
0.6436	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7055	Discontinued
0.6416	Remote Similarity	NPD8127	Discontinued
0.6415	Remote Similarity	NPD7033	Discontinued
0.6415	Remote Similarity	NPD2799	Discontinued
0.6415	Remote Similarity	NPD3748	Approved
0.6413	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6663	Approved
0.641	Remote Similarity	NPD8032	Phase 2
0.6407	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7458	Discontinued
0.6403	Remote Similarity	NPD5909	Discontinued
0.6387	Remote Similarity	NPD6039	Approved
0.6386	Remote Similarity	NPD920	Approved
0.637	Remote Similarity	NPD1989	Approved
0.6364	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5736	Approved
0.6358	Remote Similarity	NPD5494	Approved
0.6352	Remote Similarity	NPD2569	Approved
0.6352	Remote Similarity	NPD2567	Approved
0.6351	Remote Similarity	NPD7009	Phase 2
0.635	Remote Similarity	NPD7798	Approved
0.635	Remote Similarity	NPD2066	Phase 3
0.6346	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2313	Discontinued
0.634	Remote Similarity	NPD3266	Approved
0.634	Remote Similarity	NPD3267	Approved
0.634	Remote Similarity	NPD6362	Approved
0.6335	Remote Similarity	NPD1471	Phase 3
0.6331	Remote Similarity	NPD6386	Approved
0.6331	Remote Similarity	NPD6385	Approved
0.6331	Remote Similarity	NPD7411	Suspended
0.6329	Remote Similarity	NPD230	Phase 1
0.6328	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4359	Approved
0.631	Remote Similarity	NPD3226	Approved
0.6299	Remote Similarity	NPD2798	Approved
0.6299	Remote Similarity	NPD2788	Approved
0.6292	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD4807	Approved
0.6291	Remote Similarity	NPD4806	Approved
0.6289	Remote Similarity	NPD6653	Approved
0.6284	Remote Similarity	NPD7610	Discontinued
0.628	Remote Similarity	NPD2354	Approved
0.6279	Remote Similarity	NPD3882	Suspended
0.6279	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2198	Approved
0.6275	Remote Similarity	NPD2199	Approved
0.6272	Remote Similarity	NPD4380	Phase 2
0.6267	Remote Similarity	NPD5305	Approved
0.6267	Remote Similarity	NPD5306	Approved
0.6267	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD4307	Phase 2
0.6265	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1932	Approved
0.6257	Remote Similarity	NPD7460	Discontinued
0.625	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD8462	Phase 1
0.6242	Remote Similarity	NPD3268	Approved
0.6235	Remote Similarity	NPD2346	Discontinued
0.6228	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD4106	Approved
0.6225	Remote Similarity	NPD4136	Approved
0.6225	Remote Similarity	NPD4135	Approved
0.6224	Remote Similarity	NPD2329	Discontinued
0.6222	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8166	Discontinued
0.622	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3750	Approved
0.622	Remote Similarity	NPD2575	Approved
0.6215	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8285	Discontinued
0.6211	Remote Similarity	NPD1510	Phase 2
0.6207	Remote Similarity	NPD919	Approved
0.6203	Remote Similarity	NPD7714	Approved
0.6203	Remote Similarity	NPD7715	Approved
0.6203	Remote Similarity	NPD4870	Approved
0.6203	Remote Similarity	NPD6233	Phase 2
0.6199	Remote Similarity	NPD7029	Discontinued
0.6196	Remote Similarity	NPD1549	Phase 2
0.6194	Remote Similarity	NPD5647	Approved
0.619	Remote Similarity	NPD4766	Approved
0.6188	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD7768	Phase 2
0.6184	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5237	Approved
0.6181	Remote Similarity	NPD5235	Approved
0.6181	Remote Similarity	NPD5236	Approved
0.6181	Remote Similarity	NPD5239	Approved
0.6181	Remote Similarity	NPD5240	Approved
0.618	Remote Similarity	NPD7473	Discontinued
0.6178	Remote Similarity	NPD7095	Approved
0.6173	Remote Similarity	NPD2438	Suspended
0.6173	Remote Similarity	NPD2935	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data